The Real Deal Vacation package to northern California includes airfare from Chicago to San Francisco; three nights at the Flamingo Conference Resort & Spa in Santa Rosa (within an hour of both Napa and Sonoma); two nights in San Francisco at the King George Hotel; and a four-day car rental with unlimited mileage, roadside assistance, all sales taxes, surcharges, and fees; from $699 per person including all hotel and air taxes and fees.

Why It's a Deal A recent Kayak search shows the lowest round-trip airfare between Chicago and San Francisco starts at $293 in early January. Add to that $209 per person not including taxes for three nights at the Flamingo Conference Resort & Spa, and $161 per person including taxes for two nights at the King George Hotel, and you're already spending $663 on airfare and accommodations alone. For just $36 more than that, this travel package gives you the same perks, plus a four-day car rental, and covers all taxes and fees.

More Upgrade your rental car to an intermediate vehicle for from $15 more per couple, a full-size vehicle for from $35 more per couple, or a full-size SUV for from $181 more per couple.

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As seen on TV! We've followed Don Draper for seven seasons as he's crisscrossed the globe, be it via Cadillac or TWA flight. As the final episodes air, we're taking you back to the Golden Age of travel with a 'Mad Men'-inspired vacation guide for retro-style trips to cities Don visited.